Cheap flights from Canada to Chicago

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Boston (BOS)
Chicago (CHI)
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How to find the cheapest flight from
Canada to Chicago (CHI)

How far in advance should I book a flight from Canada to Chicago?

Users have found that booking a flight from Canada to Chicago at least 34 days early can save you up to 86% on average compared to booking a flight this week. If booking 34 days before your flight isn’t an option for you, users have found flights from Canada to Chicago for as little as C$ 437 when booking for a departure date within the next two weeks. You can also check prices now. Some users have found airline tickets as low as C$ 592 for flights departing within the next 3 days.

What is the cheapest month to fly from Canada to Chicago?

April can be a great time to fly to Chicago from Canada with a flight ticket averaging about C$ 318. Cheapflights users have found deals in the month of April for as cheap as C$ 241. The most expensive prices can be found in the month of January.

Cheap flights from Canada to Chicago in April, May 2021

23 May - 15 Jun
C$ 373pp
YYZ
Toronto Pearson Intl
Air Canada
Direct
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Air Canada
Direct
YYZ
Toronto Pearson Intl
23 Apr - 6 Jun
C$ 374pp
YYZ
Toronto Pearson Intl
United Airlines
Direct
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
United Airlines
Direct
YYZ
Toronto Pearson Intl
23 May - 9 Jun
C$ 378pp
YYZ
Toronto Pearson Intl
Air Canada
Direct
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Air Canada
 
1 STOP
YYZ
Toronto Pearson Intl

Canada to Chicago 2021 flight deals

23 Jul - 6 Aug
C$ 349pp
YYZ
Toronto Pearson Intl
Air Canada
Direct
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Air Canada
Direct
YYZ
Toronto Pearson Intl
23 Jul - 6 Aug
C$ 352pp
YTZ
Toronto Island
Porter Airlines
Direct
MDW
Chicago Midway
MDW
Chicago Midway
Porter Airlines
Direct
YTZ
Toronto Island
23 Jul - 6 Aug
C$ 359pp
YYZ
Toronto Pearson Intl
Air Canada
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Air Canada
Direct
YYZ
Toronto Pearson Intl

Direct flights to Chicago from Canada

23 Jul - 6 Aug
C$ 349pp
YYZ
Toronto Pearson Intl
Air Canada
Direct
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Air Canada
Direct
YYZ
Toronto Pearson Intl
23 Jul - 6 Aug
C$ 352pp
YTZ
Toronto Island
Porter Airlines
Direct
MDW
Chicago Midway
MDW
Chicago Midway
Porter Airlines
Direct
YTZ
Toronto Island
8 Sep - 12 Sep
C$ 360pp
YTZ
Toronto Island
Porter Airlines
Direct
MDW
Chicago Midway
MDW
Chicago Midway
Porter Airlines
Direct
YTZ
Toronto Island

Last minute flights from Canada to Chicago

14 Apr - 20 May
C$ 421pp
YYZ
Toronto Pearson Intl
Air Canada
Direct
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Air Canada
Direct
YYZ
Toronto Pearson Intl
14 Apr - 21 Apr
C$ 422pp
YYZ
Toronto Pearson Intl
Air Canada
Direct
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Air Canada
Direct
YYZ
Toronto Pearson Intl
14 Apr - 20 May
C$ 427pp
YYZ
Toronto Pearson Intl
Air Canada
Direct
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Air Canada
 
1 STOP
YYZ
Toronto Pearson Intl

One-way flights to Chicago from Canada

3:00 a.m. - 9:04 a.m.
United Airlines
Direct
4h 04m
YVR - ORD
United Airlines
C$ 213
United
9:15 a.m. - 10:00 a.m.
Porter Airlines
Direct
1h 45m
YTZ - MDW
Porter Airlines
C$ 215
KAYAK
5:00 p.m. - 5:38 a.m.
Air Canada
1 stop
13h 38m
YYZ - ORD
Air Canada
C$ 230
Gotogate

Related info for your journey

Flight FAQs

From Canada to Chicago

Can I find flights from Canada to Chicago for under C$ 378 on Cheapflights?

Yes, there are multiple flights from Canada to Chicago for under C$ 378. The cheapest flight booked recently is on Air Canada for just C$ 349, but on average you can expect to pay C$ 373.

What safety measures are being taken by airlines flying from Canada to Chicago to control the spread of COVID-19?

New policies can now be found on Alaska Airlines and Delta to help keep travellers safe while flying. Airline carriers are regularly disinfecting and sanitizing their aircraft. Masks are provided and are mandatory while on board. Pre-flight testing for symptoms and antibodies, alongside socially-distanced seating (for a limited time) will work towards keeping travellers safer while flying from Canada to Chicago. Policies will vary by airline.

Which airlines flying from Canada to Chicago have flexible cancellations due to COVID-19?

Some of our airline partners flying from Canada to Chicago have new flexible policies in place due to COVID-19. Air Canada, United Airlines, and American Airlines are some of the carriers where you may find flexible cancellation policies. You can use our site to filter for airlines like Air Canada with this kind of flexibility.

Are there direct flights from Canada to Chicago for under C$ 378 on Cheapflights?

Cheapflights has 20 direct flights from Canada to Chicago under C$ 378. A good price for a direct flight from Canada to Chicago is less than C$ 382.

Are there last-minute flights available from Canada to Chicago for under C$ 504?

There are currently 20+ open flights from Canada to Chicago within the next 7 days for less than C$ 504.

What are the most popular airlines that fly from Canada to Chicago?

When booking a flight from Canada to Chicago, you may want to consider flying on American Airlines, Air Canada or Alaska Airlines as they are the most popular for this route.

What are the most popular routes from Canada to Chicago?

The most popular flight routes from Canada to Chicago are Montreal Pierre Elliott Trudeau Intl - Chicago O'Hare Intl, Toronto Pearson Intl - Chicago O'Hare Intl and Vancouver Intl - Chicago O'Hare Intl.

What are the cheapest flights from Canada to Chicago?

The cheapest flight price from Canada to Chicago is C$ 256. On average you can expect to pay C$ 799. The most popular route, (Montreal Pierre Elliott Trudeau Intl - Chicago O'Hare Intl), can usually be booked for C$ 508.

How long is the flight from Canada to Chicago?

A quick flight from Canada to Chicago can take about 1h 47m. Porter Airlines provides one of the quickest options available for as low as C$ 352. Generally, flights for this route are direct.

What are the cheapest airlines to flying from Canada to Chicago round-trip?

Currently priced at C$ 350, Air Canada will fly you from Canada to Chicago and back. In addition to Air Canada, many other airlines offer competitively priced options for your trip. Search Cheapflights for deals from Porter Airlines and United Airlines - these airlines can fly you to your destination from C$ 352 and C$ 375, respectively.

What are the cheapest airlines to fly from Canada to Chicago one-way?

One-way options have recently been found by users for as low as C$ 187 on Air Canada. Other airlines that offer cheap prices include Porter Airlines from C$ 202 and Delta from C$ 213 one-way.

Destination information for Chicago

Today's exchange rate
C$ 1 = $0.80
Flight duration
2h 14m
Average temperature for April in Chicago
17.0 °C
Avg rainfall for April in Chicago
58.0 mm

Airports servicing Chicago

Chicago Midway (MDW)
Rockford (RFD)

Top 9 airlines flying from Canada to Chicago

Airline Cheapest Average Flexibility On-time COVID-19 safety
Frontier
C$ 182 C$ 268 No cancel fee 62%
Search Frontier flights
Porter Airlines
C$ 199 C$ 299 No cancel fee 52%
Search Porter Airlines flights
Alaska Airlines
C$ 132 C$ 323 No cancel fee 75%
Search Alaska Airlines flights
American Airlines
C$ 130 C$ 363 No cancel fee 71%
Search American Airlines flights
WestJet
C$ 177 C$ 368 No cancel fee 60%
Search WestJet flights
Delta
C$ 148 C$ 377 No cancel fee N/A
Search Delta flights
Air Canada
C$ 140 C$ 378 No cancel fee 67%
Search Air Canada flights
United Airlines
C$ 176 C$ 437 No cancel fee 69%
Search United Airlines flights
Aer Lingus
C$ 289 C$ 472 No cancel fee N/A
Search Aer Lingus flights
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